CA2077245C - Fungicidal compositions - Google Patents
Fungicidal compositions Download PDFInfo
- Publication number
- CA2077245C CA2077245C CA002077245A CA2077245A CA2077245C CA 2077245 C CA2077245 C CA 2077245C CA 002077245 A CA002077245 A CA 002077245A CA 2077245 A CA2077245 A CA 2077245A CA 2077245 C CA2077245 C CA 2077245C
- Authority
- CA
- Canada
- Prior art keywords
- triazol
- methyl
- ethanol
- zol
- tria
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 19
- 239000004480 active ingredient Substances 0.000 claims abstract description 32
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 22
- 241000233866 Fungi Species 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 claims abstract description 8
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims abstract description 8
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940049953 phenylacetate Drugs 0.000 claims abstract description 6
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 claims abstract description 5
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims abstract description 5
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims abstract description 5
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 claims abstract description 5
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 claims abstract description 5
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000005757 Cyproconazole Substances 0.000 claims abstract description 5
- 239000005787 Flutriafol Substances 0.000 claims abstract description 5
- 239000005795 Imazalil Substances 0.000 claims abstract description 5
- 239000005813 Penconazole Substances 0.000 claims abstract description 5
- 239000005820 Prochloraz Substances 0.000 claims abstract description 5
- 239000005839 Tebuconazole Substances 0.000 claims abstract description 5
- 239000005840 Tetraconazole Substances 0.000 claims abstract description 5
- 239000005846 Triadimenol Substances 0.000 claims abstract description 5
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 claims abstract description 5
- 229960002125 enilconazole Drugs 0.000 claims abstract description 5
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 claims abstract description 5
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 claims abstract description 5
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 claims abstract description 5
- OVFHHJZHXHZIHT-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)quinazolin-4-one Chemical compound ClC1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1N1N=CN=C1 OVFHHJZHXHZIHT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005760 Difenoconazole Substances 0.000 claims abstract description 4
- 239000005822 Propiconazole Substances 0.000 claims abstract description 4
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims abstract description 4
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 3
- -1 difem-conazole Chemical compound 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000417 fungicide Substances 0.000 claims description 9
- 230000002195 synergetic effect Effects 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 4
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 description 10
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- 241001480061 Blumeria graminis Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 230000001586 eradicative effect Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 240000000111 Saccharum officinarum Species 0.000 description 2
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- 241000219094 Vitaceae Species 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
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- 239000007859 condensation product Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4130298.2 | 1991-09-12 | ||
| DE4130298A DE4130298A1 (de) | 1991-09-12 | 1991-09-12 | Fungizide mischungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2077245A1 CA2077245A1 (en) | 1993-03-13 |
| CA2077245C true CA2077245C (en) | 2002-11-26 |
Family
ID=6440413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002077245A Expired - Lifetime CA2077245C (en) | 1991-09-12 | 1992-08-31 | Fungicidal compositions |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US5260326A (enExample) |
| EP (1) | EP0531837B1 (enExample) |
| JP (1) | JP3363482B2 (enExample) |
| AT (1) | ATE135885T1 (enExample) |
| AU (1) | AU652855B2 (enExample) |
| CA (1) | CA2077245C (enExample) |
| DE (2) | DE4130298A1 (enExample) |
| DK (1) | DK0531837T3 (enExample) |
| ES (1) | ES2085526T3 (enExample) |
| GR (1) | GR3019613T3 (enExample) |
| IL (1) | IL102997A (enExample) |
| NZ (1) | NZ244289A (enExample) |
| TW (1) | TW223003B (enExample) |
| ZA (1) | ZA926921B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9202378D0 (en) * | 1992-02-05 | 1992-03-18 | Sandoz Ltd | Inventions relating to fungicidal compositions |
| DE4233337A1 (de) * | 1992-10-05 | 1994-04-07 | Bayer Ag | Mikrobizide Mittel |
| DE4309272A1 (de) * | 1993-03-23 | 1994-09-29 | Basf Ag | Fungizide Mischung |
| DE4321206A1 (de) * | 1993-06-25 | 1995-01-05 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| US5436248A (en) * | 1993-07-02 | 1995-07-25 | Ciba-Geigy Corporation | Microbicides |
| JP3634409B2 (ja) * | 1993-09-13 | 2005-03-30 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
| ATE136734T1 (de) * | 1993-09-24 | 1996-05-15 | Basf Ag | Fungizide mischungen |
| EP0648417B1 (de) * | 1993-09-24 | 1996-12-04 | BASF Aktiengesellschaft | Fungizide Mischungen |
| ATE136729T1 (de) * | 1993-09-24 | 1996-05-15 | Basf Ag | Fungizide mischungen |
| DK0645084T3 (da) * | 1993-09-24 | 1996-08-26 | Basf Ag | Fungicide blandinger |
| AU1120495A (en) | 1993-12-02 | 1995-06-19 | Sumitomo Chemical Company, Limited | Bactericidal composition |
| AU1280095A (en) * | 1993-12-27 | 1995-07-17 | Sumitomo Chemical Company, Limited | Bactericidal composition |
| TW286264B (enExample) | 1994-05-20 | 1996-09-21 | Ciba Geigy Ag | |
| ATE184153T1 (de) * | 1994-06-10 | 1999-09-15 | Basf Ag | Fungizide mischungen |
| DE4444911A1 (de) * | 1994-12-16 | 1996-06-27 | Basf Ag | Fungizide Mischung |
| EP0820232A1 (de) * | 1995-04-08 | 1998-01-28 | Basf Aktiengesellschaft | Synergistische fungizide zusammensetzungen aus chinolinderivaten und cytochrom b/c-inhibitors |
| MY115814A (en) * | 1995-06-16 | 2003-09-30 | Bayer Ip Gmbh | Crop protection compositions |
| ATE184751T1 (de) * | 1995-08-17 | 1999-10-15 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit azolderivaten |
| PL329239A1 (en) * | 1996-04-11 | 1999-03-15 | Basf Ag | Fungicidal mixture |
| CA2252677C (en) * | 1996-04-26 | 2006-12-19 | Basf Aktiengesellschaft | Fungicide mixture |
| ATE215308T1 (de) * | 1996-04-26 | 2002-04-15 | Basf Ag | Fungizide mischung |
| US6319949B1 (en) | 1996-07-11 | 2001-11-20 | Syngenta Limited | Pesticidal sprays |
| WO1999000013A2 (en) * | 1997-06-30 | 1999-01-07 | Monsanto Company | Microparticles containing agricultural active ingredients |
| TW431861B (en) | 1997-12-18 | 2001-05-01 | Basf Ag | Fungicidal mixtures based on amide compounds and azoles |
| US6096769A (en) * | 1998-04-20 | 2000-08-01 | American Cyanamid Company | Fungicidal co-formulation |
| FR2789551B1 (fr) * | 1999-02-12 | 2002-06-21 | Aventis Cropscience Sa | Compositions fongicides pour la protection des fruits |
| GB9906692D0 (en) * | 1999-03-23 | 1999-05-19 | Novartis Ag | Pesticidal compositions |
| CN1646014A (zh) * | 2002-04-05 | 2005-07-27 | 巴斯福股份公司 | 基于苄胺肟衍生物和唑类的杀真菌混合物 |
| KR101038848B1 (ko) * | 2002-08-19 | 2011-06-02 | 바스프 에스이 | 카르복실산 함유 제제 및 그의 식물 재배 용도 |
| CA2505588A1 (en) * | 2002-11-15 | 2004-08-05 | Basf Aktiengesellschaft | Fungicidal mixtures based on a triazolopyrimidine derivative and azoles |
| KR100994773B1 (ko) * | 2004-03-29 | 2010-11-16 | 삼성전자주식회사 | 계층적 움직임 추정에 있어서 움직임 벡터 생성 방법 및장치 |
| AR056286A1 (es) * | 2005-03-24 | 2007-10-03 | Cheminova As | Metodo para proteger una planta de soja con flutriafol |
| US20090227450A1 (en) * | 2005-09-16 | 2009-09-10 | Basf Aktiengesellschaft | Triazole-Based Fungicidal Mixtures |
| JP2010505811A (ja) | 2006-10-04 | 2010-02-25 | ファイザー・プロダクツ・インク | カルシウム受容体アンタゴニストとしてのピリド［４，３−ｄ］ピリミジン−４（３Ｈ）−オン誘導体 |
| WO2009043686A2 (de) * | 2007-09-27 | 2009-04-09 | Basf Se | Fungizide mischungen |
| JP2011503155A (ja) * | 2007-11-16 | 2011-01-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌混合物ｉｉｉ |
| CN102210308A (zh) * | 2011-04-21 | 2011-10-12 | 陕西汤普森生物科技有限公司 | 一种含有啶氧菌酯与三唑类化合物的农药组合物 |
| CN107960408A (zh) * | 2017-12-13 | 2018-04-27 | 海南大学 | 丙环唑·氟硅唑聚乳酸缓释微球及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL78175A (en) * | 1985-03-29 | 1989-10-31 | Basf Ag | Azolylmethyloxiranes,their preparation and their use as fungicide crop protection agents |
| DE3623921A1 (de) * | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
| GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
| DE3934714A1 (de) * | 1989-10-18 | 1991-04-25 | Bayer Ag | Fungizide wirkstoffkombinationen |
| DE3935113A1 (de) * | 1989-10-21 | 1991-04-25 | Basf Ag | Fungizide mischung |
| US5859616A (en) * | 1997-04-10 | 1999-01-12 | Gec-Marconi Hazeltine Corporation | Interleaved planar array antenna system providing angularly adjustable linear polarization |
-
1991
- 1991-09-12 DE DE4130298A patent/DE4130298A1/de not_active Withdrawn
-
1992
- 1992-08-29 DE DE59205825T patent/DE59205825D1/de not_active Expired - Lifetime
- 1992-08-29 AT AT92114812T patent/ATE135885T1/de active
- 1992-08-29 EP EP92114812A patent/EP0531837B1/de not_active Expired - Lifetime
- 1992-08-29 DK DK92114812.8T patent/DK0531837T3/da active
- 1992-08-29 ES ES92114812T patent/ES2085526T3/es not_active Expired - Lifetime
- 1992-08-31 IL IL10299792A patent/IL102997A/en not_active IP Right Cessation
- 1992-08-31 CA CA002077245A patent/CA2077245C/en not_active Expired - Lifetime
- 1992-08-31 TW TW081106894A patent/TW223003B/zh not_active IP Right Cessation
- 1992-09-04 JP JP23724892A patent/JP3363482B2/ja not_active Expired - Fee Related
- 1992-09-10 NZ NZ244289A patent/NZ244289A/en not_active IP Right Cessation
- 1992-09-11 US US07/943,677 patent/US5260326A/en not_active Expired - Lifetime
- 1992-09-11 AU AU23536/92A patent/AU652855B2/en not_active Expired
- 1992-09-11 ZA ZA926921A patent/ZA926921B/xx unknown
-
1993
- 1993-07-08 US US08/087,317 patent/US5317027A/en not_active Expired - Lifetime
-
1994
- 1994-01-28 US US08/188,012 patent/US5399579A/en not_active Expired - Lifetime
- 1994-10-06 US US08/319,027 patent/US5484779A/en not_active Expired - Lifetime
-
1996
- 1996-04-09 GR GR960401008T patent/GR3019613T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL102997A0 (en) | 1993-01-31 |
| DE59205825D1 (de) | 1996-05-02 |
| IL102997A (en) | 1996-09-12 |
| JPH05221811A (ja) | 1993-08-31 |
| US5399579A (en) | 1995-03-21 |
| ES2085526T3 (es) | 1996-06-01 |
| US5260326A (en) | 1993-11-09 |
| NZ244289A (en) | 1994-06-27 |
| JP3363482B2 (ja) | 2003-01-08 |
| ATE135885T1 (de) | 1996-04-15 |
| US5484779A (en) | 1996-01-16 |
| DK0531837T3 (da) | 1996-04-22 |
| EP0531837A1 (de) | 1993-03-17 |
| DE4130298A1 (de) | 1993-03-18 |
| EP0531837B1 (de) | 1996-03-27 |
| TW223003B (enExample) | 1994-05-01 |
| ZA926921B (en) | 1994-03-11 |
| CA2077245A1 (en) | 1993-03-13 |
| GR3019613T3 (en) | 1996-07-31 |
| AU2353692A (en) | 1993-03-18 |
| AU652855B2 (en) | 1994-09-08 |
| US5317027A (en) | 1994-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |